(3aR,4R,8bR)-4-hydroxy-3,3a,4,8b-tetrahydroindeno[1,2-b]furan-2-one | 1246196-24-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 茚满类
• 英文名称: (3aR,4R,8bR)-4-hydroxy-3,3a,4,8b-tetrahydroindeno[1,2-b]furan-2-one
• CAS: 1246196-24-6
• 化学式: C₁₁H₁₀O₃
• 分子量: 190.199
• InChiKey: VGHDQTBHTHIFQP-MIMYLULJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  14
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  甲酸甲酯 、 (3aR,4R,8bR)-4-hydroxy-3,3a,4,8b-tetrahydroindeno[1,2-b]furan-2-one 在 potassium tert-butylate 作用下， 反应 3.0h， 生成
  参考文献：
  名称：

  羟基-GR24 的高度对映体富集立体异构体的合成†

  摘要：

  与仿生亲电环化级联相反，我们采用了仿生亲核环化级联，只需一步即可得到4-羟基-GR24的三环核心。使用立体选择性Noyori转移氢化的动力学拆分可实现任何对映异构体富集的4-羟基-GR24立体异构体的简明合成。

  DOI：

  10.1039/c5ob02349a
• 作为产物：
  描述：

  (3aR,4R,8bR)-2-oxo-3,3a,4,8b-tetrahydro-2H-indeno[1,2-b]furan-4-yl acetate 在 potassium carbonate 作用下， 以 甲醇 为溶剂， 以71%的产率得到(3aR,4R,8bR)-4-hydroxy-3,3a,4,8b-tetrahydroindeno[1,2-b]furan-2-one
  参考文献：
  名称：

  Synthesis of optically active strigolactones: enzymatic resolution and asymmetric hydroxylation

  摘要：

  A synthetic intermediate of an optically active strigolactone analogue was prepared in two ways: enzymatic resolution and asymmetric hydroxylation. The 4-hydroxy tricyclic lactone 4 was enzymatically resolved to give the corresponding enantiomers in an enantiomerically pure state, while the tricyclic lactone 5 was hydroxylated asymmetrically at the 4-position by the action of cytochrome P450 monooxygenase. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2010.04.016

文献信息

• Synthesis of highly enantio-enriched stereoisomers of hydroxy-GR24
  作者：J. C. Morris、C. S. P. McErlean

  DOI：10.1039/c5ob02349a

  日期：——

  In contrast to a biomimetic electrophilic cyclisation cascade, we employ a contra-biomimetic nucleophilic cyclisation cascade to give the tricyclic core of 4-hydroxy-GR24 in a single step. Kinetic resolution using a stereoselective Noyori transfer hydrogenation enables the concise synthesis of any enantiomerically enriched 4-hydroxy-GR24 stereoisomer.

  与仿生亲电环化级联相反，我们采用了仿生亲核环化级联，只需一步即可得到4-羟基-GR24的三环核心。使用立体选择性Noyori转移氢化的动力学拆分可实现任何对映异构体富集的4-羟基-GR24立体异构体的简明合成。
• Synthesis of optically active strigolactones: enzymatic resolution and asymmetric hydroxylation
  作者：Hirosato Takikawa、Hiromasa Imaishi、Aya Tanaka、Satoshi Jikumaru、Mami Fujiwara、Mitsuru Sasaki

  DOI：10.1016/j.tetasy.2010.04.016

  日期：2010.5

  A synthetic intermediate of an optically active strigolactone analogue was prepared in two ways: enzymatic resolution and asymmetric hydroxylation. The 4-hydroxy tricyclic lactone 4 was enzymatically resolved to give the corresponding enantiomers in an enantiomerically pure state, while the tricyclic lactone 5 was hydroxylated asymmetrically at the 4-position by the action of cytochrome P450 monooxygenase. (C) 2010 Elsevier Ltd. All rights reserved.